Dimethyl Sulfoxide → HCID 14010393, compound

HRID 2119184Notes

Reaction equation

HRID 2119184 reaction equation
[C:1](Cl)(=O)C(Cl)=O.CS(C)=O.C[C:12]1[C:25]([CH2:26][CH2:27][CH2:28][OH:29])=[C:24]([O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[CH:23]=[CH:22][C:13]=1[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15].C(N(CC)CC)C>C(Cl)Cl.O>[CH:28]([CH:27]([CH3:1])[CH2:26][C:25]1[CH:12]=[C:13]([CH:22]=[CH:23][C:24]=1[O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])=[O:29]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86741685HCID 86741685, compound

Product 1

HCID 14010393HCID 14010393, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
25 °C

Procedure

To a solution of 1.8 ml of oxalyl chloride in 43 ml of methylene chloride were added dropwise a solution of 3.0 ml of DMSO in 9 ml of methylene chloride at -60° C., and then a solution of 6.14 g of 3-(2-methylhydroxypropyl-4-pivaloyloxybenzophenone in 17 ml of methylene chloride. The mixture was stirred at about -50°-60° C. for 15 min, then treated with 12.1 ml of triethylamine. The reaction mixture was stirred at -50° C. for 5 min, warmed to 25° C., and then treated with 85 ml of water. The organic layer was washed with dilute hydrochloric acid and then with brine, dried (MgSO4) and concentrated to give 5.0 g of product as an oil.

Workup

  1. stirringThe reaction mixture was stirred at -50° C. for 5 min
  2. washThe organic layer was washed with dilute hydrochloric acid
  3. dry with materialwith brine, dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-82ddf8a8c5b84ffda28550ebd2d89755
Source dataset
uspto-grants-1987_07
Patent number
US04683241

Reaction notes

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